Table 4.
Entry | Conditions | Results |
---|---|---|
1 | Li, cat. naphthlene, −78 °C | debrominated products |
2 | Mg, MeOH, sonication | no reaction |
3 | Mg, MeOH, reflux | debrominated products |
4 | TBAF, THF | decomposition of 16 |
5 | hv (254 nm), CH3CN | 1 (trace) + decomposition of 16 |
6 | hv (254 nm), dry THF | decomposition of 16 |
7 | hv (254 nm), THF-H2O | decomposition of 16 |
8 | SmI2 (8 equiv), THF, 0 °C to rt | 1 (88% yield[a]) |
Isolated yield.